Hydrochloric Acid → 3-Bromo-2-fluoro-5-methylaniline
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[Br:1][C:2]1[C:3]([F:17])=[C:4]([NH:9]C(=O)OC(C)(C)C)[CH:5]=[C:6]([CH3:8])[CH:7]=1.Cl.[OH-].[Na+]>C(O)(C)C.O>[Br:1][C:2]1[C:3]([F:17])=[C:4]([CH:5]=[C:6]([CH3:8])[CH:7]=1)[NH2:9][Br:1][C:2]1[C:3]([F:17])=[C:4]([NH:9]C(=O)OC(C)(C)C)[CH:5]=[C:6]([CH3:8])[CH:7]=1.Cl.[OH-].[Na+]>C(O)(C)C.O>[Br:1][C:2]1[C:3]([F:17])=[C:4]([CH:5]=[C:6]([CH3:8])[CH:7]=1)[NH2:9]To a solution of tert-butyl 3-bromo-2-fluoro-5-methylphenylcarbamate (985 mg, 3.24 mmol) in isopropyl alcohol (10 mL) was added concentrated aqueous HCl (˜12 M, 2.6 mL, 32.4 mmol) and the reaction mixture was warmed to 60° C. for 2 hours, allowed to cool to room temperature, and then concentrated in vacuo to afford a white solid. The solid was dissolved in water and the resulting aqueous solution was neutralized with aqueous 1.0 M NaOH solution, and extracted with Et2O. The organic phase was washed with brine, dried (MgSO4) and concentrated to afford 3-bromo-2-fluoro-5-methylaniline (594 mg, 2.91 mmol, 90%) which was carried forward without further purification: 1H NMR (300 MHz, CDCl3) δ 2.21 (s, 3H) 3.71 (br s, 2H) 6.51 (d, J=7.9 Hz, 1H) 6.70 (d, J=4.7 Hz, 1H).
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